Amazon has steadily been building out a sprawling advertising business across its website, its video platforms like Amazon Fire and IMDb, and a programmatic demand-side platform that targets and places ads on websites outside Amazon.

One of Amazon's biggest advertising challenges is convincing brands like automakers and financial service providers that don't sell their products on Amazon that beyond driving conversions, it can drive awareness and loyalty. To that end, Amazon is borrowing from the playbooks of Facebook, Google, and Twitter.

Advertisers find Amazon hard to navigate because it requires them to work with various teams that don't always talk to one another. Agencies have said that the company has become more flexible but that it's clear Amazon is not dependent on advertising.

Amazon reported $10 billion in "other" revenue, mostly from advertising sales, out of total revenue of $233 billion in 2018. According to Amazon's job site, the company is hiring for more than 1,200 jobs across eight teams that live under the "advertising" umbrella. Only about 160 of the 845 jobs Amazon is hiring for in New York are in advertising.

"Retail is the core strength of Amazon, [but] there is a firewall between the retail and advertising teams," said Will Margaritis, the senior vice president of e-commerce at Dentsu Aegis Network. "There's no way to get around it, but the power of Amazon's advertising comes from their retail side."

Amazon is working to prove that its platform can work for big brands, particularly in programmatic and over-the-top advertising. The goal is to "help brands tell a story in the Amazon shopping experience that resonates with consumers and feeds into longer-term relationship," Colleen Aubrey, the global vice president of performance advertising at Amazon, told Business Insider recently.

"They're where Facebook was circa 2014 or 2013," said George Manas, the president and chief media officer at OMD. "They are aggressively trying to move up the funnel and become a place for consumers to go that isn't just a last-click solution to buying something."

Amazon is trying out its version of a dog and pony show

Facebook, Google, Twitter, Snap, and Pinterest all have big New York teams that woo agencies with new programs and features. Over the past year, agencies say, Amazon has followed suit by growing a similar team with reps dedicated to specific agencies.

Tech platforms are known for treating ad executives to fancy dinners or tickets to sports games, but at Amazon, whose CEO and founder, Jeff Bezos, is known for his frugality, the advertising push is more subdued, several agency execs said.

"Their budgets for the dog and pony show are absolutely smaller than a lot of the other vendors, which is fine," Margaritis said. "They let the products speak for themselves. But they're not flying anyone out to Aspen — Amazon is going to take you out to a nice lunch."

Amazon also routinely visits agencies to pitch its advertising business. During a recent visit with the Brooklyn, New York-based agency Huge, Amazon talked about how its platform put consumers, not advertisers, first. Amazon also played up its data and video efforts in its pitch, said Jenna Massaroni, the director of comms design at Huge.

"They're trying to [be] almost altruistic," she said.

But Amazon's data is a better fit for e-commerce and performance-minded marketers than big brands, she said. The company plays up its shopper data but not broader behavioral and demographic data that big brands care about.

"People are hesitant about putting money into Amazon when the full scale of their targeting capabilities are not known," Massaroni said. "I almost think that they're more of a competitor to programmatic companies."

Amazon doesn't have a full-blown advertising leader — yet

One area where Amazon diverges from Facebook is in its leadership.

Agency sources rattled off a short list of execs who they're regularly in contact with at Amazon including Aubrey; the vice president of global advertising sales and marketing, Seth Dallaire; and Ryan Mayward, the global head of agency development. Amazon also assigns executives and account-management staffers to companies to help with advertising needs.

But several people paused when asked whether Amazon had its own version of Carolyn Everson, the Facebook executive who serves as the face of the company's ad business and has helped Facebook's revenue balloon since joining the company in 2011.

"I wouldn't say that they have an Everson there — I don't know that Amazon would handle it that way just given that advertising isn't their main business right now," one agency executive said.

Agencies were mixed on whether Amazon needed an executive to champion advertising, but Huge's Massaroni said it could make a difference with big clients who want to associate a face with a company.

"These big companies need to have that rallying person to get everyone excited," she said.

Agencies are starting to get their hands on more proof points

Amazon offers agencies accreditation programs to become certified in advertising and puts on trainings that can last from 30 minutes on ad format basics to four hours for an in-depth education on specific ad formats. Dentsu Aegis Network's Margaritis said the agency recently got a deep dive into Amazon's product that prints ad messages on Amazon shipping boxes.

Facebook, Twitter, Google, and Snap also provide trainings and certifications for advertisers. In exchange for becoming certified, agencies stay up to date on Amazon's products and get first dibs on new ad formats.

Agencies say Amazon has gotten better at sharing case studies of successful campaigns. But they say the data can be thin.

"Right now, it's Amazon saying, 'Trust us, we know this works,'" said Margaritis, who'd like to see more data about commercials that air in streams of Thursday-night NFL games. "Brands want to know exactly what they're getting, and when some of these features are brand new, it can take some convincing to get a brand to put [money] into the big, shiny Amazon bucket."